Table of contents

1. A Review of General Chemistry5h 5m
2. Molecular Representations1h 14m
3. Acids and Bases2h 46m
4. Alkanes and Cycloalkanes4h 17m
5. Chirality3h 39m
6. Thermodynamics and Kinetics1h 22m
7. Substitution Reactions1h 48m
8. Elimination Reactions2h 30m
9. Alkenes and Alkynes2h 9m
10. Addition Reactions3h 19m
11. Radical Reactions1h 58m
12. Alcohols, Ethers, Epoxides and Thiols2h 42m
13. Alcohols and Carbonyl Compounds2h 17m
14. Synthetic Techniques1h 26m
15. Analytical Techniques:IR, NMR, Mass Spect7h 3m
16. Conjugated Systems6h 13m
17. Ultraviolet Spectroscopy51m
18. Aromaticity2h 34m
19. Reactions of Aromatics: EAS and Beyond5h 1m
20. Phenols55m
21. Aldehydes and Ketones: Nucleophilic Addition4h 56m
22. Carboxylic Acid Derivatives: NAS2h 51m
23. The Chemistry of Thioesters, Phophate Ester and Phosphate Anhydrides1h 10m
24. Enolate Chemistry: Reactions at the Alpha-Carbon1h 53m
25. Condensation Chemistry2h 9m
26. Amines1h 43m
27. Heterocycles2h 0m
28. Carbohydrates5h 53m
29. Amino Acids4h 20m
30. Peptides and Proteins2h 42m
31. Catalysis in Organic Reactions1h 30m
32. Lipids 2h 50m
33. The Organic Chemistry of Metabolic Pathways2h 52m
34. Nucleic Acids1h 32m
35. Transition Metals6h 14m
36. Synthetic Polymers1h 49m

21. Aldehydes and Ketones: Nucleophilic Addition

Nitrile to Ketone

Organic Chemistry

21. Aldehydes and Ketones: Nucleophilic Addition

Nitrile to Ketone

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2:37 minutes

Problem 39b

Textbook Question

Show how each transformation may be accomplished by using a nitrile as an intermediate. You may use any necessary reagents.
(b) cyclohexanecarboxamide → cyclohexyl ethyl ketone

Verified step by step guidance

Identify the starting material and the target product. The starting material is cyclohexanecarboxamide, and the target product is cyclohexyl ethyl ketone. The goal is to use a nitrile as an intermediate in the transformation.

Convert the starting material (cyclohexanecarboxamide) into a nitrile. This can be achieved by dehydrating the amide using a dehydrating agent such as phosphorus pentoxide (P₂O₅) or thionyl chloride (SOCl₂). This step will yield cyclohexanecarbonitrile.

Perform a Grignard reaction to introduce the ethyl group. React cyclohexanecarbonitrile with ethylmagnesium bromide (C₂H₅MgBr) in an ether solvent. This step will form an imine intermediate.

Hydrolyze the imine intermediate to yield the ketone. Use aqueous acid (e.g., H₃O⁺) to hydrolyze the imine, resulting in cyclohexyl ethyl ketone.

Verify the structure of the product to ensure it matches the target compound, cyclohexyl ethyl ketone. This completes the transformation using a nitrile as an intermediate.

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Key Concepts

Here are the essential concepts you must grasp in order to answer the question correctly.

Nitrile Chemistry

Nitriles are organic compounds containing a cyano group (-C≡N). They can be converted into various functional groups through hydrolysis, reduction, or other transformations. Understanding the reactivity of nitriles is crucial for using them as intermediates in organic synthesis, as they can be transformed into amides, carboxylic acids, or ketones depending on the reagents and conditions applied.

Amide to Ketone Transformation

The conversion of an amide to a ketone can be achieved through a series of reactions, often involving the formation of a nitrile intermediate. This process typically includes the dehydration of the amide to form a nitrile, followed by hydrolysis or other reactions to yield the desired ketone. Recognizing the steps involved in this transformation is essential for successfully synthesizing cyclohexyl ethyl ketone from cyclohexanecarboxamide.

Reagents and Reaction Conditions

The choice of reagents and reaction conditions is critical in organic synthesis. For the transformation in question, reagents such as phosphorus oxychloride (POCl3) or thionyl chloride (SOCl2) may be used to convert the amide to a nitrile. Additionally, understanding the role of reducing agents or hydrolytic conditions is necessary to facilitate the final conversion to the ketone, ensuring the correct pathway is followed for the desired product.

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